I run a transit authority and a statewide medical transportation brokerage. I’m also building a small company, working a piece of land, and raising two boys. Every one of those fronts generates paper — email, filings, meeting notes, manuals, receipts, ideas — and for years, the paper won more days than I did.
The standard executive answer is delegation, and I delegate plenty. But there’s a category of information work you can’t hand off: the cross-domain stuff. The email that touches both the budget and a board relationship. The article that matters to the business you’re building, not the one you run. Nobody else can file that for you, because nobody else lives at the intersection.
So I built a system that does.
Not a chatbot — an operator
The core is unglamorous: a vault of a few thousand plain-text notes, organized by domain, sitting on my own machine. What makes it work is the operator — an AI agent that runs on a schedule, follows a written rulebook, and does the filing whether I’m at the desk or not.
The distinction matters. Most people use AI like a vending machine: walk up, ask a question, walk away. I wanted the opposite — a system with standing orders. Overnight it reads the intake channels, summarizes what arrived, links each item to what it relates to, and routes it to its home. By the time I pour coffee, the triage that used to eat my first ninety minutes is a briefing I can read in five.
The rules that keep it honest
An unattended system operating on your life needs discipline more than it needs intelligence. Mine runs on a few hard rules:
- Failures loud, successes silent. A job that breaks must announce itself. A job that works shouldn’t need my attention.
- One canonical location per concept. The moment two notes claim to be the truth, the system is lying to you somewhere.
- The human owns the blast radius. The system files, drafts, and proposes. Anything irreversible — anything that leaves the house — waits for me.
Those rules came from running operations, not from software. A brokerage coordinating medical trips at scale teaches you exactly what happens when a process fails silently. I just applied the same standard to my own desk.
What it actually changed
Honestly? My mornings, and my attention. The volume of information didn’t shrink — it grows every year. What changed is what it costs me. Filing costs me nothing now. Finding costs me nothing. What’s left is the part that was always the real job: judgment.
I’m writing more about the architecture on the project page, and this site itself came out of the system — which is about the best proof of work I can offer.